HU200583B - Process for producing unsaturated carboxylic acids with 2e, 4e configuration - Google Patents
Process for producing unsaturated carboxylic acids with 2e, 4e configuration Download PDFInfo
- Publication number
- HU200583B HU200583B HU854023A HU402385A HU200583B HU 200583 B HU200583 B HU 200583B HU 854023 A HU854023 A HU 854023A HU 402385 A HU402385 A HU 402385A HU 200583 B HU200583 B HU 200583B
- Authority
- HU
- Hungary
- Prior art keywords
- isomerization
- formula
- acid
- trimethyl
- methoxy
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 34
- 150000001735 carboxylic acids Chemical class 0.000 title claims abstract description 7
- 238000006317 isomerization reaction Methods 0.000 claims abstract description 29
- 150000003863 ammonium salts Chemical class 0.000 claims abstract description 25
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- 239000000155 melt Substances 0.000 claims abstract description 9
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 7
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 6
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 239000012442 inert solvent Substances 0.000 claims abstract description 3
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 claims description 37
- 239000002253 acid Substances 0.000 claims description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 20
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 14
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000002516 radical scavenger Substances 0.000 claims description 5
- 150000002148 esters Chemical class 0.000 claims description 3
- 239000003574 free electron Substances 0.000 claims description 3
- 150000003464 sulfur compounds Chemical class 0.000 claims description 3
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 238000011065 in-situ storage Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000000926 separation method Methods 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims 1
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 9
- 125000003545 alkoxy group Chemical group 0.000 abstract description 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 2
- 239000001257 hydrogen Substances 0.000 abstract description 2
- 238000004817 gas chromatography Methods 0.000 description 20
- MNYBEULOKRVZKY-QQZWAFJOSA-N (2z,4e)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoic acid Chemical compound COC(C)(C)CCCC(C)C\C=C\C(\C)=C/C(O)=O MNYBEULOKRVZKY-QQZWAFJOSA-N 0.000 description 18
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229910021529 ammonia Inorganic materials 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- QMVSVDPAWIVPNR-YMOPAIQUSA-N (2e,4e)-3,7,11-trimethyldodeca-2,4-dienoic acid Chemical compound CC(C)CCCC(C)C\C=C\C(\C)=C\C(O)=O QMVSVDPAWIVPNR-YMOPAIQUSA-N 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- -1 11- methoxy-7,7.11-trimethyl-2Z, 4E-dodecadienoic acid Chemical compound 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- GUUVPOWQJOLRAS-UHFFFAOYSA-N Diphenyl disulfide Chemical compound C=1C=CC=CC=1SSC1=CC=CC=C1 GUUVPOWQJOLRAS-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000002955 isolation Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000007348 radical reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- MNYBEULOKRVZKY-TZOAMJEDSA-N (2e,4e)-11-methoxy-3,7,11-trimethyldodeca-2,4-dienoic acid Chemical compound COC(C)(C)CCCC(C)C\C=C\C(\C)=C\C(O)=O MNYBEULOKRVZKY-TZOAMJEDSA-N 0.000 description 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 1
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000029052 metamorphosis Effects 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Die Erfindung betrifft ein Verfahren zur Herstellung von Carbonsaeuren der 2E,4E-Stereokonfiguration der allgemeinen Formel I, (worin X Wasserstoff, Hydroxy oder C1-4 Alkoxy bedeutet) durch Isomerisierung von Carbonsaeuren der 2Z,4E-Konfiguration der allgemeinen Formel VII, (worin X die obige Bedeutung hat). Erfindungsgemaess wird die 2Z,4E-Carbonsaeure der allgemeinen Formel VII oder ein Alkali- oder Ammoniumsalz davon in der Schmelze oder in Anwesenheit eines inerten Loesungsmittels in Gegenwart eines Katalysators isomerisiert und danach aus dem Isomerengemisch der Carbonsaeuren der allgemeinen Formel I und VII oder der Alkali- oder Ammoniumsalze davon die Carbonsaeure der allgemeinen Formel I ohne Entfernung des Katalysators in Form des Ammoniumsalzes abgetrennt. Formel I und VII
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU854023A HU200583B (en) | 1985-10-18 | 1985-10-18 | Process for producing unsaturated carboxylic acids with 2e, 4e configuration |
| IT22043/86A IT1197887B (it) | 1985-10-18 | 1986-10-17 | Procedimento per la preparazione di acidi 2e, 4e carbossilici |
| NL8602620A NL8602620A (nl) | 1985-10-18 | 1986-10-17 | Werkwijze voor de bereiding van 2e,4e-carbonzuren. |
| GB8624988A GB2181732B (en) | 1985-10-18 | 1986-10-17 | Process for the preparation of 2e 4e carboxylic acids |
| JP61245615A JPS62181233A (ja) | 1985-10-18 | 1986-10-17 | ２ｅ，４ｅ−カルボン酸の製造方法 |
| ES8602656A ES2002040A6 (es) | 1985-10-18 | 1986-10-17 | Procedimiento de preparacion de acidos 2e,4e carboxilicos |
| DD86295359A DD253994A5 (de) | 1985-10-18 | 1986-10-17 | Verfahren zur herstellung von carbonsaeuren der 2e,4e-konfiguration |
| YU01767/86A YU176786A (en) | 1985-10-18 | 1986-10-17 | Process for obtaining 2e, 4e carboxylic acids |
| FR8614425A FR2588862A1 (fr) | 1985-10-18 | 1986-10-17 | Procede de preparation d'acides 2e, 4e-carboxyliques |
| FI864219A FI864219A (fi) | 1985-10-18 | 1986-10-17 | Foerfarande foer framstaellning av 2e,4e -karboxylsyror. |
| CS867543A CS268682B2 (en) | 1985-10-18 | 1986-10-17 | Method of 2e, 4e dodecadiene acids production |
| DE3635613A DE3635613A1 (de) | 1985-10-18 | 1986-10-20 | Verfahren zur herstellung von, gegebenenfalls in der 11-stellung substiuierten, 3,7,11-tri-(methyl)-2e,4e-dodecadiensaeuren |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU854023A HU200583B (en) | 1985-10-18 | 1985-10-18 | Process for producing unsaturated carboxylic acids with 2e, 4e configuration |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| HUT41725A HUT41725A (en) | 1987-05-28 |
| HU200583B true HU200583B (en) | 1990-07-28 |
Family
ID=10966563
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU854023A HU200583B (en) | 1985-10-18 | 1985-10-18 | Process for producing unsaturated carboxylic acids with 2e, 4e configuration |
Country Status (12)
| Country | Link |
|---|---|
| JP (1) | JPS62181233A (de) |
| CS (1) | CS268682B2 (de) |
| DD (1) | DD253994A5 (de) |
| DE (1) | DE3635613A1 (de) |
| ES (1) | ES2002040A6 (de) |
| FI (1) | FI864219A (de) |
| FR (1) | FR2588862A1 (de) |
| GB (1) | GB2181732B (de) |
| HU (1) | HU200583B (de) |
| IT (1) | IT1197887B (de) |
| NL (1) | NL8602620A (de) |
| YU (1) | YU176786A (de) |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3818047A (en) * | 1972-08-07 | 1974-06-18 | C Henrick | Substituted pyrones |
| FR2265714A1 (en) * | 1974-03-26 | 1975-10-24 | Zoecon Corp | 3,7,11-Trimethyl-2,4,11-dodecatrienoic acid and derivs. - with juvenile hormone insecticidal activity |
-
1985
- 1985-10-18 HU HU854023A patent/HU200583B/hu not_active IP Right Cessation
-
1986
- 1986-10-17 GB GB8624988A patent/GB2181732B/en not_active Expired
- 1986-10-17 ES ES8602656A patent/ES2002040A6/es not_active Expired
- 1986-10-17 FR FR8614425A patent/FR2588862A1/fr active Pending
- 1986-10-17 YU YU01767/86A patent/YU176786A/xx unknown
- 1986-10-17 JP JP61245615A patent/JPS62181233A/ja active Pending
- 1986-10-17 IT IT22043/86A patent/IT1197887B/it active
- 1986-10-17 CS CS867543A patent/CS268682B2/cs unknown
- 1986-10-17 DD DD86295359A patent/DD253994A5/de not_active IP Right Cessation
- 1986-10-17 FI FI864219A patent/FI864219A/fi not_active IP Right Cessation
- 1986-10-17 NL NL8602620A patent/NL8602620A/nl not_active Application Discontinuation
- 1986-10-20 DE DE3635613A patent/DE3635613A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| FR2588862A1 (fr) | 1987-04-24 |
| DD253994A5 (de) | 1988-02-10 |
| ES2002040A6 (es) | 1988-07-01 |
| HUT41725A (en) | 1987-05-28 |
| DE3635613A1 (de) | 1987-04-23 |
| GB8624988D0 (en) | 1986-11-19 |
| IT1197887B (it) | 1988-12-21 |
| FI864219A (fi) | 1987-04-19 |
| IT8622043A0 (it) | 1986-10-17 |
| GB2181732B (en) | 1989-09-27 |
| CS268682B2 (en) | 1990-04-11 |
| YU176786A (en) | 1988-06-30 |
| NL8602620A (nl) | 1987-05-18 |
| FI864219A0 (fi) | 1986-10-17 |
| GB2181732A (en) | 1987-04-29 |
| CS754386A2 (en) | 1989-07-12 |
| JPS62181233A (ja) | 1987-08-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HMM4 | Cancellation of final prot. due to non-payment of fee |